catena-Poly[[[(2-phenyl-acetato-κO)zinc(II)]bis-[μ-4,4'-(disulfanedi-yl)dipyridine-κN:N']] monohydrate].

In the title compound, {[Zn(C(8)H(7)O(2))(2)(C(10)H(8)N(2)S(2))(2)]·H(2)O}(n), the Zn(II) atom is coordinated by four N atoms from four 4,4'-(disulfanedi-yl)dipyridine (bpds) ligands and two O atoms from two 2-phenyl-acetate anions in a distorted octa-hedral coordination geometry. The two bpds ligands of the same axial chirality bridge Zn(II) atoms, generating repeated rhomboidal chains, which are linked by O-H⋯O hydrogen bonds into a ladder structure.

Related literature

For coordination chemistry based on pyridyl donor ligands, see: Biradha et al. (2006 ▶); Liu et al. (2008 ▶); Hernández-Ahuactzi et al. (2008 ▶); Ma, Wang, Wang et al. (2009 ▶). For bpds compounds, see: Horikoshi & Mochida (2006 ▶); Carballo et al. (2008 ▶); Ma, Wang, Hu et al. (2009 ▶); Horikoshi & Mikuriya (2005 ▶). For compounds containing phenyl­acetic acid, see: Johnston et al. (2008 ▶).

Experimental

Crystal data

[Zn(C8H7O2)2(C10H8N2S2)2]·H2O

M = 794.27

Triclinic,

a = 9.851 (2) Å

b = 11.130 (2) Å

c = 18.319 (4) Å

α = 90.38 (3)°

β = 98.88 (3)°

γ = 115.89 (3)°

V = 1779.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.97 mm−1

T = 295 K

0.51 × 0.41 × 0.36 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.623, T max = 0.701

16701 measured reflections

7859 independent reflections

6036 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.07

7859 reflections

451 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.34 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021331/er2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021331/er2078Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C8H7O2)2(C10H8N2S2)2]·H2O	Z = 2
Mr = 794.27	F(000) = 820
Triclinic, P1	Dx = 1.483 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.851 (2) Å	Cell parameters from 16701 reflections
b = 11.130 (2) Å	θ = 3.1–27.5°
c = 18.319 (4) Å	µ = 0.97 mm−1
α = 90.38 (3)°	T = 295 K
β = 98.88 (3)°	Block, colorless
γ = 115.89 (3)°	0.51 × 0.41 × 0.36 mm
V = 1779.0 (6) Å3

Rigaku R-AXIS RAPID diffractometer	7859 independent reflections
Radiation source: fine-focus sealed tube	6036 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→14
Tmin = 0.623, Tmax = 0.701	l = −23→23
16701 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.3693P] where P = (Fo2 + 2Fc2)/3
7859 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Zn	0.42078 (3)	0.23364 (2)	0.254511 (13)	0.03328 (8)
N1	0.21801 (19)	0.10323 (18)	0.17515 (9)	0.0351 (4)
C1	0.1234 (2)	0.1508 (2)	0.14209 (11)	0.0353 (5)
H1A	0.1526	0.2422	0.1492	0.042*
C2	−0.0162 (2)	0.0710 (2)	0.09761 (12)	0.0355 (5)
H2A	−0.0790	0.1081	0.0755	0.043*
C3	−0.0604 (2)	−0.0650 (2)	0.08669 (11)	0.0336 (5)
C4	0.0375 (3)	−0.1155 (2)	0.12028 (14)	0.0457 (6)
H4A	0.0115	−0.2064	0.1141	0.055*
C5	0.1747 (3)	−0.0276 (2)	0.16317 (14)	0.0463 (6)
H5A	0.2407	−0.0617	0.1850	0.056*
S1	−0.24164 (6)	−0.16230 (6)	0.03032 (3)	0.03988 (14)
S2	−0.24204 (6)	−0.34128 (6)	0.00746 (3)	0.04027 (14)
C6	−0.3406 (2)	−0.4474 (2)	0.07251 (11)	0.0344 (5)
C7	−0.3961 (3)	−0.4103 (2)	0.12877 (13)	0.0476 (6)
H7A	−0.3824	−0.3226	0.1357	0.057*
C8	−0.4725 (3)	−0.5053 (2)	0.17481 (13)	0.0466 (6)
H8A	−0.5116	−0.4795	0.2118	0.056*
N2	−0.4932 (2)	−0.63104 (18)	0.16917 (9)	0.0339 (4)
C9	−0.4425 (2)	−0.6675 (2)	0.11302 (12)	0.0377 (5)
H9A	−0.4595	−0.7563	0.1069	0.045*
C10	−0.3665 (2)	−0.5801 (2)	0.06409 (12)	0.0377 (5)
H10A	−0.3330	−0.6094	0.0260	0.045*
N3	0.61670 (19)	0.37405 (18)	0.33457 (10)	0.0355 (4)
C11	0.5949 (2)	0.4081 (2)	0.40060 (12)	0.0358 (5)
H11A	0.4977	0.3640	0.4128	0.043*
C12	0.7090 (2)	0.5050 (2)	0.45119 (12)	0.0359 (5)
H12A	0.6889	0.5262	0.4962	0.043*
C13	0.8547 (2)	0.5704 (2)	0.43370 (11)	0.0335 (5)
C14	0.8780 (2)	0.5378 (2)	0.36502 (12)	0.0398 (5)
H14A	0.9735	0.5818	0.3509	0.048*
C15	0.7571 (2)	0.4390 (2)	0.31818 (12)	0.0415 (5)
H15A	0.7740	0.4163	0.2726	0.050*
S3	0.99682 (6)	0.69153 (6)	0.50235 (3)	0.04202 (15)
S4	1.20007 (6)	0.72797 (6)	0.47202 (3)	0.04384 (15)
C16	1.2462 (2)	0.8675 (2)	0.41869 (11)	0.0339 (5)
C17	1.1450 (2)	0.9135 (2)	0.38416 (12)	0.0379 (5)
H17A	1.0420	0.8714	0.3883	0.046*
C18	1.2001 (2)	1.0225 (2)	0.34368 (13)	0.0402 (5)
H18A	1.1317	1.0540	0.3214	0.048*
N4	1.34608 (19)	1.08651 (18)	0.33422 (10)	0.0357 (4)
C19	1.4430 (2)	1.0421 (2)	0.36901 (12)	0.0393 (5)
H19A	1.5457	1.0869	0.3644	0.047*
C20	1.3994 (2)	0.9344 (2)	0.41103 (12)	0.0381 (5)
H20A	1.4707	0.9066	0.4339	0.046*
O1	0.29666 (17)	0.33877 (16)	0.27800 (8)	0.0414 (4)
O2	0.2410 (2)	0.3097 (2)	0.39220 (9)	0.0544 (5)
C21	0.2319 (3)	0.3518 (2)	0.33031 (13)	0.0389 (5)
C22	0.1335 (4)	0.4250 (4)	0.31603 (16)	0.0678 (9)
H22A	0.0295	0.3630	0.3204	0.081*
H22B	0.1692	0.4966	0.3551	0.081*
C23	0.1282 (3)	0.4843 (3)	0.24333 (15)	0.0494 (6)
C24	0.2307 (3)	0.6123 (3)	0.23429 (19)	0.0666 (8)
H24A	0.3012	0.6656	0.2750	0.080*
C25	0.2315 (5)	0.6642 (4)	0.1657 (2)	0.0866 (11)
H25A	0.3032	0.7509	0.1605	0.104*
C26	0.1280 (6)	0.5887 (6)	0.1063 (2)	0.0942 (13)
H26A	0.1294	0.6230	0.0601	0.113*
C27	0.0224 (5)	0.4634 (5)	0.1139 (2)	0.0892 (12)
H27A	−0.0500	0.4121	0.0732	0.107*
C28	0.0224 (4)	0.4120 (3)	0.18197 (19)	0.0687 (8)
H28A	−0.0513	0.3259	0.1866	0.082*
O3	0.57013 (19)	0.14005 (17)	0.23618 (8)	0.0453 (4)
O4	0.5095 (3)	0.0218 (2)	0.12864 (11)	0.0731 (6)
C29	0.5861 (3)	0.0632 (2)	0.19184 (13)	0.0426 (5)
C30	0.7158 (4)	0.0237 (3)	0.21550 (17)	0.0652 (8)
H30A	0.7119	−0.0377	0.1765	0.078*
H30B	0.8123	0.1035	0.2188	0.078*
C31	0.7172 (3)	−0.0404 (3)	0.28744 (15)	0.0469 (6)
C32	0.6281 (3)	−0.1760 (3)	0.28977 (17)	0.0618 (7)
H32A	0.5654	−0.2267	0.2466	0.074*
C33	0.6295 (4)	−0.2379 (3)	0.35429 (19)	0.0706 (8)
H33A	0.5680	−0.3294	0.3543	0.085*
C34	0.7211 (4)	−0.1654 (3)	0.41871 (18)	0.0663 (8)
H34A	0.7226	−0.2070	0.4625	0.080*
C35	0.8096 (4)	−0.0319 (3)	0.41752 (18)	0.0669 (8)
H35A	0.8717	0.0182	0.4610	0.080*
C36	0.8088 (3)	0.0305 (3)	0.35277 (17)	0.0605 (7)
H36A	0.8710	0.1219	0.3532	0.073*
O5	0.3132 (3)	−0.1386 (2)	−0.00858 (12)	0.0856 (7)
H5C	0.3720	−0.0885	−0.0334	0.128*
H5D	0.3676	−0.1044	0.0305	0.128*

	U11	U22	U33	U12	U13	U23
Zn	0.03625 (14)	0.03132 (15)	0.02738 (13)	0.01058 (10)	0.00539 (10)	0.00328 (10)
N1	0.0369 (9)	0.0334 (10)	0.0314 (9)	0.0130 (8)	0.0037 (7)	0.0012 (8)
C1	0.0399 (11)	0.0305 (12)	0.0318 (11)	0.0115 (9)	0.0082 (9)	0.0051 (9)
C2	0.0368 (11)	0.0356 (13)	0.0333 (11)	0.0150 (9)	0.0071 (9)	0.0074 (9)
C3	0.0330 (10)	0.0357 (12)	0.0280 (10)	0.0101 (9)	0.0095 (8)	0.0065 (9)
C4	0.0469 (13)	0.0306 (13)	0.0532 (15)	0.0148 (10)	−0.0018 (11)	−0.0016 (11)
C5	0.0451 (13)	0.0415 (15)	0.0502 (15)	0.0213 (11)	−0.0035 (11)	−0.0019 (11)
S1	0.0346 (3)	0.0371 (3)	0.0383 (3)	0.0079 (2)	0.0035 (2)	0.0064 (2)
S2	0.0414 (3)	0.0367 (3)	0.0326 (3)	0.0064 (2)	0.0119 (2)	0.0028 (2)
C6	0.0305 (10)	0.0361 (12)	0.0299 (11)	0.0087 (8)	0.0052 (8)	0.0044 (9)
C7	0.0703 (16)	0.0278 (12)	0.0451 (14)	0.0171 (11)	0.0255 (12)	0.0053 (10)
C8	0.0664 (16)	0.0365 (14)	0.0415 (13)	0.0211 (11)	0.0271 (12)	0.0061 (11)
N2	0.0400 (9)	0.0293 (10)	0.0302 (9)	0.0128 (7)	0.0085 (7)	0.0043 (7)
C9	0.0453 (12)	0.0363 (13)	0.0319 (11)	0.0186 (10)	0.0064 (9)	0.0033 (9)
C10	0.0437 (12)	0.0403 (13)	0.0323 (11)	0.0198 (10)	0.0117 (9)	0.0034 (10)
N3	0.0365 (9)	0.0358 (11)	0.0327 (10)	0.0151 (8)	0.0049 (7)	0.0008 (8)
C11	0.0371 (11)	0.0359 (12)	0.0329 (11)	0.0138 (9)	0.0086 (9)	0.0051 (9)
C12	0.0457 (12)	0.0333 (12)	0.0289 (11)	0.0169 (9)	0.0088 (9)	0.0050 (9)
C13	0.0400 (11)	0.0277 (11)	0.0313 (11)	0.0148 (9)	0.0026 (9)	0.0064 (9)
C14	0.0337 (11)	0.0425 (14)	0.0389 (12)	0.0129 (9)	0.0066 (9)	0.0007 (10)
C15	0.0382 (12)	0.0495 (15)	0.0356 (12)	0.0177 (10)	0.0084 (9)	−0.0034 (10)
S3	0.0443 (3)	0.0374 (3)	0.0313 (3)	0.0071 (2)	0.0037 (2)	0.0024 (2)
S4	0.0408 (3)	0.0383 (3)	0.0477 (3)	0.0154 (2)	0.0009 (2)	0.0144 (3)
C16	0.0394 (11)	0.0294 (12)	0.0305 (11)	0.0140 (9)	0.0036 (9)	0.0038 (9)
C17	0.0320 (11)	0.0377 (13)	0.0421 (13)	0.0129 (9)	0.0085 (9)	0.0107 (10)
C18	0.0376 (11)	0.0454 (14)	0.0421 (13)	0.0218 (10)	0.0088 (10)	0.0140 (11)
N4	0.0365 (9)	0.0342 (10)	0.0350 (10)	0.0136 (8)	0.0084 (8)	0.0078 (8)
C19	0.0312 (10)	0.0495 (15)	0.0341 (12)	0.0149 (10)	0.0062 (9)	0.0055 (10)
C20	0.0348 (11)	0.0452 (14)	0.0362 (12)	0.0203 (10)	0.0035 (9)	0.0070 (10)
O1	0.0494 (9)	0.0504 (10)	0.0324 (8)	0.0286 (8)	0.0101 (7)	0.0016 (7)
O2	0.0647 (11)	0.0735 (13)	0.0402 (10)	0.0405 (10)	0.0204 (8)	0.0146 (9)
C21	0.0413 (12)	0.0386 (13)	0.0377 (12)	0.0171 (10)	0.0113 (10)	0.0019 (10)
C22	0.092 (2)	0.087 (2)	0.0610 (18)	0.0650 (19)	0.0367 (17)	0.0286 (16)
C23	0.0567 (15)	0.0557 (17)	0.0517 (15)	0.0366 (13)	0.0176 (12)	0.0113 (13)
C24	0.0659 (18)	0.060 (2)	0.073 (2)	0.0278 (15)	0.0109 (15)	0.0058 (16)
C25	0.103 (3)	0.067 (2)	0.111 (3)	0.048 (2)	0.043 (3)	0.041 (2)
C26	0.134 (4)	0.133 (4)	0.068 (2)	0.102 (3)	0.028 (3)	0.033 (3)
C27	0.093 (3)	0.123 (4)	0.065 (2)	0.068 (3)	−0.0098 (19)	−0.012 (2)
C28	0.0663 (18)	0.060 (2)	0.081 (2)	0.0295 (15)	0.0121 (16)	−0.0011 (17)
O3	0.0613 (10)	0.0496 (10)	0.0361 (9)	0.0325 (8)	0.0156 (8)	0.0069 (8)
O4	0.0900 (15)	0.0695 (15)	0.0499 (12)	0.0298 (11)	0.0025 (10)	−0.0152 (10)
C29	0.0546 (14)	0.0338 (13)	0.0398 (13)	0.0164 (10)	0.0189 (11)	0.0083 (10)
C30	0.080 (2)	0.072 (2)	0.0706 (19)	0.0493 (17)	0.0411 (16)	0.0242 (16)
C31	0.0523 (14)	0.0432 (15)	0.0565 (15)	0.0286 (11)	0.0183 (12)	0.0071 (12)
C32	0.0708 (18)	0.0469 (17)	0.0577 (18)	0.0215 (14)	−0.0027 (14)	−0.0036 (14)
C33	0.086 (2)	0.0390 (17)	0.078 (2)	0.0230 (14)	0.0032 (17)	0.0111 (15)
C34	0.081 (2)	0.075 (2)	0.0628 (19)	0.0527 (18)	0.0094 (16)	0.0146 (17)
C35	0.0722 (19)	0.070 (2)	0.0612 (19)	0.0390 (17)	−0.0052 (15)	−0.0109 (16)
C36	0.0598 (16)	0.0419 (16)	0.075 (2)	0.0192 (12)	0.0097 (14)	−0.0055 (15)
O5	0.0779 (14)	0.0842 (17)	0.0699 (15)	0.0144 (12)	0.0105 (11)	−0.0102 (12)

Zn—O1	2.1105 (15)	C17—C18	1.371 (3)
Zn—N4i	2.160 (2)	C17—H17A	0.9300
Zn—N1	2.180 (2)	C18—N4	1.338 (3)
Zn—N2ii	2.1808 (19)	C18—H18A	0.9300
Zn—N3	2.186 (2)	N4—C19	1.338 (3)
Zn—O3	2.2019 (16)	N4—Znii	2.160 (2)
N1—C5	1.332 (3)	C19—C20	1.371 (3)
N1—C1	1.333 (3)	C19—H19A	0.9300
C1—C2	1.386 (3)	C20—H20A	0.9300
C1—H1A	0.9300	O1—C21	1.270 (2)
C2—C3	1.383 (3)	O2—C21	1.235 (3)
C2—H2A	0.9300	C21—C22	1.512 (4)
C3—C4	1.385 (3)	C22—C23	1.494 (4)
C3—S1	1.776 (2)	C22—H22A	0.9700
C4—C5	1.381 (3)	C22—H22B	0.9700
C4—H4A	0.9300	C23—C24	1.369 (4)
C5—H5A	0.9300	C23—C28	1.375 (4)
S1—S2	2.0311 (10)	C24—C25	1.387 (5)
S2—C6	1.770 (2)	C24—H24A	0.9300
C6—C7	1.377 (3)	C25—C26	1.351 (6)
C6—C10	1.387 (3)	C25—H25A	0.9300
C7—C8	1.381 (3)	C26—C27	1.351 (6)
C7—H7A	0.9300	C26—H26A	0.9300
C8—N2	1.324 (3)	C27—C28	1.376 (5)
C8—H8A	0.9300	C27—H27A	0.9300
N2—C9	1.343 (3)	C28—H28A	0.9300
N2—Zni	2.1808 (19)	O3—C29	1.251 (3)
C9—C10	1.376 (3)	O4—C29	1.242 (3)
C9—H9A	0.9300	C29—C30	1.528 (4)
C10—H10A	0.9300	C30—C31	1.504 (4)
N3—C15	1.335 (3)	C30—H30A	0.9700
N3—C11	1.341 (3)	C30—H30B	0.9700
C11—C12	1.375 (3)	C31—C36	1.379 (4)
C11—H11A	0.9300	C31—C32	1.380 (4)
C12—C13	1.387 (3)	C32—C33	1.373 (4)
C12—H12A	0.9300	C32—H32A	0.9300
C13—C14	1.387 (3)	C33—C34	1.372 (4)
C13—S3	1.773 (2)	C33—H33A	0.9300
C14—C15	1.376 (3)	C34—C35	1.357 (4)
C14—H14A	0.9300	C34—H34A	0.9300
C15—H15A	0.9300	C35—C36	1.379 (4)
S3—S4	2.0294 (10)	C35—H35A	0.9300
S4—C16	1.764 (2)	C36—H36A	0.9300
C16—C17	1.382 (3)	O5—H5C	0.8098
C16—C20	1.392 (3)	O5—H5D	0.8029
O1—Zn—N4i	97.17 (7)	C17—C16—S4	126.14 (17)
O1—Zn—N1	87.04 (7)	C20—C16—S4	115.38 (17)
N4i—Zn—N1	88.63 (7)	C18—C17—C16	118.5 (2)
O1—Zn—N2ii	88.99 (7)	C18—C17—H17A	120.7
N4i—Zn—N2ii	173.74 (7)	C16—C17—H17A	120.7
N1—Zn—N2ii	90.57 (7)	N4—C18—C17	124.0 (2)
O1—Zn—N3	88.99 (7)	N4—C18—H18A	118.0
N4i—Zn—N3	92.71 (7)	C17—C18—H18A	118.0
N1—Zn—N3	175.94 (7)	C19—N4—C18	116.7 (2)
N2ii—Zn—N3	88.51 (7)	C19—N4—Znii	119.65 (14)
O1—Zn—O3	174.45 (6)	C18—N4—Znii	122.96 (15)
N4i—Zn—O3	84.12 (7)	N4—C19—C20	123.7 (2)
N1—Zn—O3	98.39 (7)	N4—C19—H19A	118.2
N2ii—Zn—O3	89.85 (7)	C20—C19—H19A	118.2
N3—Zn—O3	85.56 (7)	C19—C20—C16	118.6 (2)
C5—N1—C1	117.18 (19)	C19—C20—H20A	120.7
C5—N1—Zn	122.60 (15)	C16—C20—H20A	120.7
C1—N1—Zn	119.88 (15)	C21—O1—Zn	137.60 (16)
N1—C1—C2	123.3 (2)	O2—C21—O1	126.2 (2)
N1—C1—H1A	118.4	O2—C21—C22	116.3 (2)
C2—C1—H1A	118.4	O1—C21—C22	117.5 (2)
C3—C2—C1	118.7 (2)	C23—C22—C21	117.5 (2)
C3—C2—H2A	120.6	C23—C22—H22A	107.9
C1—C2—H2A	120.6	C21—C22—H22A	107.9
C2—C3—C4	118.5 (2)	C23—C22—H22B	107.9
C2—C3—S1	116.61 (17)	C21—C22—H22B	107.9
C4—C3—S1	124.88 (18)	H22A—C22—H22B	107.2
C5—C4—C3	118.4 (2)	C24—C23—C28	116.9 (3)
C5—C4—H4A	120.8	C24—C23—C22	121.5 (3)
C3—C4—H4A	120.8	C28—C23—C22	121.6 (3)
N1—C5—C4	123.9 (2)	C23—C24—C25	121.4 (3)
N1—C5—H5A	118.1	C23—C24—H24A	119.3
C4—C5—H5A	118.1	C25—C24—H24A	119.3
C3—S1—S2	104.60 (9)	C26—C25—C24	119.9 (4)
C6—S2—S1	105.51 (8)	C26—C25—H25A	120.1
C7—C6—C10	118.0 (2)	C24—C25—H25A	120.1
C7—C6—S2	125.76 (19)	C25—C26—C27	120.2 (4)
C10—C6—S2	116.21 (16)	C25—C26—H26A	119.9
C6—C7—C8	119.0 (2)	C27—C26—H26A	119.9
C6—C7—H7A	120.5	C26—C27—C28	119.8 (4)
C8—C7—H7A	120.5	C26—C27—H27A	120.1
N2—C8—C7	123.7 (2)	C28—C27—H27A	120.1
N2—C8—H8A	118.2	C23—C28—C27	121.9 (3)
C7—C8—H8A	118.2	C23—C28—H28A	119.1
C8—N2—C9	117.00 (19)	C27—C28—H28A	119.1
C8—N2—Zni	121.68 (14)	C29—O3—Zn	143.09 (17)
C9—N2—Zni	120.90 (15)	O4—C29—O3	125.0 (2)
N2—C9—C10	123.3 (2)	O4—C29—C30	117.4 (2)
N2—C9—H9A	118.4	O3—C29—C30	117.5 (2)
C10—C9—H9A	118.4	C31—C30—C29	117.2 (2)
C9—C10—C6	118.9 (2)	C31—C30—H30A	108.0
C9—C10—H10A	120.5	C29—C30—H30A	108.0
C6—C10—H10A	120.5	C31—C30—H30B	108.0
C15—N3—C11	117.28 (19)	C29—C30—H30B	108.0
C15—N3—Zn	122.71 (14)	H30A—C30—H30B	107.3
C11—N3—Zn	119.66 (14)	C36—C31—C32	117.1 (3)
N3—C11—C12	123.3 (2)	C36—C31—C30	122.5 (3)
N3—C11—H11A	118.4	C32—C31—C30	120.3 (3)
C12—C11—H11A	118.4	C33—C32—C31	121.7 (3)
C11—C12—C13	118.72 (19)	C33—C32—H32A	119.2
C11—C12—H12A	120.6	C31—C32—H32A	119.2
C13—C12—H12A	120.6	C34—C33—C32	120.3 (3)
C14—C13—C12	118.5 (2)	C34—C33—H33A	119.9
C14—C13—S3	125.30 (17)	C32—C33—H33A	119.9
C12—C13—S3	116.18 (16)	C35—C34—C33	118.9 (3)
C15—C14—C13	118.6 (2)	C35—C34—H34A	120.6
C15—C14—H14A	120.7	C33—C34—H34A	120.6
C13—C14—H14A	120.7	C34—C35—C36	120.9 (3)
N3—C15—C14	123.5 (2)	C34—C35—H35A	119.5
N3—C15—H15A	118.2	C36—C35—H35A	119.5
C14—C15—H15A	118.2	C31—C36—C35	121.1 (3)
C13—S3—S4	105.43 (8)	C31—C36—H36A	119.5
C16—S4—S3	106.12 (8)	C35—C36—H36A	119.5
C17—C16—C20	118.5 (2)	H5C—O5—H5D	95.1

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5c···O4iii	0.81	2.20	2.970 (3)	158
O5—H5d···O4	0.80	2.15	2.945 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5c⋯O4i	0.81	2.20	2.970 (3)	158
O5—H5d⋯O4	0.80	2.15	2.945 (3)	169

Symmetry code: (i) .